反応式
[F:1][C:2]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]2[CH:3]1[CH:4]([OH:9])[CH2:5][C:6]2=[O:8].[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].CN(C)C=O.N1C=CN=C1>O>[F:1][C:2]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:3]2[CH:7]1[CH:6]([O:8][Si:19]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:22])[CH3:21])[CH2:5][C:4]2=[O:9]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 1
実験手順
2.8 g of (1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-hydroxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate and 2.5 g of t-butyldimethylchlorosilane were dissolved into 14 ml of N,N-dimethylformamide. 1.0 g of imidazole was further added thereto with ice-cooling, and this was stirred at room temperature for one day. The reaction solution was poured into water, and extracted with n-hexane-ethyl acetate (1:9). The obtained organic layer was washed with, in sequence, water and a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. After filtering off the desiccant, concentration of the filtrate was carried out under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=15:1), yielding 3.8 g of (1RS,4SR,5SR,6RS)ethyl 6-fluoro-4-t-butyldimethylsilyloxy-2-oxobicyclo[3.1.0]hexane-6-carboxylate. The proton NMR and mass spectrograph data are shown below.
後処理
- temperaturewith ice-cooling
- extractionextracted with n-hexane-ethyl acetate (1:9)
- washThe obtained organic layer was washed with, in sequence, water
- dry with materiala saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate
- filtrationAfter filtering off the desiccant, concentration of the filtrate
- customThe residue was purified by column chromatography (silica gel: Wako gel (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=15:1)
出典と根拠
- ORDレコード
- ord-a84c11ef540746c0baf4c5edf220658f
- 出典データセット
- uspto-grants-2001_12
- 特許番号
- US06333428B1
関連ノート
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